


An Unhealthy Obsession: Hurt

by Sheiladine



Series: An Unhealthy Obsession [4]
Category: The Simpsons
Genre: F/M
Language: English
Status: In-Progress
Published: 2017-03-20
Updated: 2017-05-11
Packaged: 2018-10-08 06:43:13
Rating: Explicit
Warnings: Graphic Depictions Of Violence, Rape/Non-Con
Chapters: 3
Words: 3,387
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/10380786
Author URL: https://archiveofourown.org/users/Sheiladine/pseuds/Sheiladine
Summary: Lisa wants to win back Jimbo's heart in her own way, but will it work or is it too late? How will Lisa's decisions effect her future? This is one of three endings I've written for An Unhealthy Obsession.





	1. Chapter 1

Chapter 1

                 Lisa Simpson was excited to finally be left alone for an entire week. She cunningly told her parents that her art retreat was one week longer than it actually was, and without much effort convinced them to go on a family trip they had been planning without her. Being home alone gave her a whimsical feeling. No mom, no dad, no Maggie and no Bart! Lisa, recently turning 18, had been craving some very much wanted privacy. She racked her brain with thoughts of what she could do alone, like what books she could read, what music she could play... but only after a long day filled with a bus ride and unpacking she decided to just go out for a brisk evening walk instead. Lisa decided that she would wear a low cut orange summer dress with a short, red denim jacket with some red sandals since it was a nice temperate day, and bolted off.

                Lisa knew that she could go on walks by herself even when her family was around, but something about coming home to nobody around made her feel fresh and excited, and made the short trip around the block even more refreshing.

            On her walk she spotted someone that gained her full attention, James "Jimbo" Jones. Lisa had always had an interest in him, but alas, age had always made her stand her ground in this timeline... until now that is. Although she had a close relationship with him as Leah when she travelled time, she had nearly no interaction with him as _Lisa Simpson_. Lisa watched him as he walked down the street, slouched over with his hands in his pockets. Lisa decided to bashfully head toward him. Once she was close she stopped directly in front of him. He looked up at her suspiciously and then in annoyance. No member of the Simpson family has a reason to talk to him, especially not Bart's nerdy little sister.

"H-hello!" Lisa stammered while forcing a nervous smile.

"Uh... hey." Jimbo replied. He looked at her suspiciously wondering what she could be up to by talking to him. 

"Nice weather we’re having today isn't it? Heh... heh." She continued to smile awkwardly.

            Jimbo looked at her in confusion for a moment before the feeling of annoyance washed over him again and he and proceeded to try and walk around her. He didn't feel like causing her any trouble, and he didn't want her to cause him trouble. As things stood now, she was just a nuisance.

"W-wait!" Lisa exclaimed, quickly grabbing him by the arm as an attempt to get him to stop.

            Jimbo looked at her questioningly, still suspicious of what she was trying to pull. He didn't say anything, and continued to look at her waiting for a response.

"D-do you want to come over? To my house I mean... my family is gone and all so..."

"Huh... why?" He asked, more suspicious than ever.

"Just... well... do you want to or not?!" Lisa exclaimed bashfully.

Jimbo looked at her in bewilderment, but decided to go along with whatever she was planning.

"I guess."

            Lias winced as he spoke then looked up at him in a bit of girlish excitement. She hurriedly took him by the hand and took him home.


	2. Who Are You?

Chapter 2

            Jimbo had been inside of Lisa’s house many times before. He had had occasional flings with the babysitters who used to watch Lisa and her brother Bart. The house isn't what made him nervous though, it was _her_ , Lisa Simpson. She somehow talked him into coming over to her house with a seemingly unknown motive. Lisa, a nerd, plus Bart's little sister. _Nothing good could come of this_ he thought.

"Do you want anything? I can get you somethingif you w-want!..." Lisa stammered.

"Whatever." Jimbo replied.

            He dropped onto the couch in the living room where he then turned on the television. He had been here before, but nevertheless he felt uneasy.

            Lisa returned to him with two of her father's beers. Jimbo looked at her with a slight hint of amusement. He took one and casually opened it, then looked back at her to see what she would do. Lisa was eyeing the can, carefully opening it. She timidly drank from it, the taste was reminding her of that cold fall when she first shared a beer with him and they kissed until her lips nearly went numb... Jimbo was surprised to see Lisa drinking a beer; she didn't seem like the type. He tried to pretend he didn't notice, but he couldn't help but noticing how she looked almost sad.

            For a while they both just sat on the couch watching television, correction, he watched while she kept glancing over at him nervously every few seconds. Lisa tried inching closer to him until their thighs barely touched, but from what she could tell he could care less as she glanced at him staring obliviously into the television. Jimbo on the other hand was thinking to himself about how he must be just imagining her getting closer to him and tried to ignore her.

            Lisa was feeling extremely frustrated on the inside. _Isn't this how things were supposed to happen? Home alone, just the two of them closing in on each other on the sofa._ _What am I missing here? Wasn't he interested? He had to be to come over to her house, right?_ _Maybe I’m just not being bold enough._ Thoughts continued to race through her head. It was so much easier a few years ago, much so that she didn't understand it. Lisa finally decided to take a risk, lifted her hand and gently put it on his thigh.

            Jimbo pretended to ignore it, or her, who may as well be an it as far as he was concerned. _Does she know what she was doing? She can’t_ he thought. She has to be too young, also she reminded him somewhat of _her_... but Lisa was obviously a lot younger and more of a nerd. He tried his best to brush off his thoughts and concluded that she must not know what she's doing. 

            Lisa quickly realized that he wasn't reacting to her advances. She thought that she must be trying to move things to subtly. She moved closer to him, close enough that she knew he must be able to notice her, then she leaned against him while still keeping her hand on top of his thigh. She thought he looked a little nervous, but she couldn't tell for sure since she was nervous herself. Being that close to him brought familiar feelings inside of her that she hadn't felt in years. She had butterflies in her stomach, she could smell his familiar scent, she liked it, and she liked how she could smell the faint aroma of cigarettes on him. 

            Jimbo now knew for sure that she knew what she was doing. There was no way he could mistake what she was doing as just pure ignorance. She was nuzzling and clinging right onto him for fucks sake. He couldn't risk it. She is too young and looks too much like _her_. He had to, with regret, stop her. He didn’t want to deal with the drama of a young girl, especially if she was potentially under-aged and could get him jailed.

"Uh, Lisa I don't think you should..."

"What, why?" Lisa sat up quickly. She knew something was going wrong, but what? Wasn't she good enough? Pretty enough?

"Maybe if you were older..." Jimbo mumbled.

            Lisa looked at him in bewilderment.

"What do you mean by that? _I just turned eighteen_!"

"Wha..." He started to say, looking at her in slight shock. This was new information...

"I know I'm still young b-Aah-!" Lisa was cut off by Jimbo roughly pushing her over so she was lying on her back on the couch, and so he was on top of her. She couldn't protest even if she wanted to since her lips were now forcefully locked with his. 

            Lisa was surprised for a moment, but didn't protest. She returned his advances. She slipped her hands up his shirt and felt his bare back. She was instantly reminded of how great of a kisser he was, and a wave of bottled up emotions flew through her body.  Jimbo always seemed to know what he was doing with her... He slid his hand up her dress caressing her inner thigh.

            Lisa was in emotional ecstasy, but she was not having as much fun on a couch as she thought she could in her room... she was finally able to get a word in between the groping and making out to make a suggestion.

"I-ahh-think we should move to my room." She gasped. 

            Jimbo nodded and let her get herself back off the couch as she led the two of them up the stairs and to her room. He watched her eagerly in a new light as she walked up the stairs in her short tight dress. He felt as if he really dodged a bullet with this one. It did beg the question though, why was a nerd like her interested in a dirtbag like him for? He decided he would worry about that later. He would focus on getting tail now.

            Lisa dropped herself onto her bed and stretched out on it. She didn't want to throw off her jacket in fear of revealing her tattoo... it would reveal too much and she didn't have a good explanation for it.

            Jimbo greedily eyed her lying on the bed. He admired her figure momentarily before jumping her bones. He proceeded to kiss her, and slid his hands back up her dress to roughly fondle her backside.

            Lisa felt amazingly good, but one thought kept stirring in the back of her head. How far would this go? She guessed that she would be having sex with him, but it felt like it had been so long since she had last done so, and she still felt worried.

            Jimbo was still on top of her, but stood up on his knees and started fiddling with the button and zipper on his jeans before returning to kissing and fondling her. After a while it was clear that he was tired of feeling through her panties so he slipped them off of her. Lisa became inexplicitly bashful, mostly because she hadn't done this in so long and she didn’t know what he thought of her now, but she could feel him hardening as he grinded up against her.

            Jimbo stopped momentarily to pull down the front of his pants enough to reveal his cock, and to her surprise he entered her without much warning. She let out a slight cry of pain before wrapping her arms around him as he fucked her. _When did he get so rough?_ She thought to herself. However, she felt the physical pleasure she missed for so long, but something just felt off. She felt empty. Regardless, he was still able to get her to orgasm, partially because she wanted him so bad. The sex didn’t last long and it was obvious that he didn’t care if it did or not, and he didn’t seem to care if she felt anything or not. He came inside of her then rolled over next to her, lying on his back casually. This upset her since there was no emotion in this.

            Lisa tried to nuzzle up against him, feeling a bit euphoric. He got out a pack cigarettes and a lighter he dug out of the pockets in his jeans. He casually took one out and lit it up, taking a drag. Lisa looked at him with a slight look of disgust and responded,

"You shouldn't smoke, it’s bad for you."

            Jimbo just smirked at her and blew smoke in her face. She winced a bit, she hadn't touched a cigarette in years either. He smiled a bit wider and held the lit cigarette up to her implying she should use it. She looked at him incredulously for a moment, hesitated, then inhaled from it deeply while he was still holding it and slowly exhaled shuddering. He laughed at her in response replying,

"I was just egging you on. You didn't have to. Surprised you did.”

            Lisa stared at him bitterly as he took another drag. She turned back over holding his left, free hand and nuzzled herself back into him.

            He didn't get it. She was the last person he'd imagine banging, not out of dislike, but just because it was so out of character on both sides. The rebel without a cause with the weird, quirky (yet cute) nerd.  _How the hell did this happen?_ He thought. She also reminded him so much of _her_ for some reason, but probably because they look somewhat alike. Also, he didn't ever picture her smoking. _Is she doing this for show?_ He wondered.

"What's your motive?" Jimbo asked.

"I have no idea what you're talking about." Lisa replied slightly dazed, continuing to snuggle against him. She grabbed the cigarette from him and started to smoke it. She didn’t clue him into the slightest as to why she was doing this.

"So you're home alone and wanted to fuck some random guy you barely know, huh? I don't buy it."

            Lisa blushed a bit and replied hesitantly,

"No, you're right to not believe that because that wasn't what I was doing..."

            This caused more confusion for him than ever. With such negative and limited reactions they've had in the past, what could possibly be her reason for choosing him to fuck around with?

"Then why in the hell would such a goody-goody nerd like you gain from getting fucked by a scumbag like me?" Jimbo scowled before taking the cigarette and putting it out on the top of her bedside table, leaving a smudged burn mark. Lisa looked away from him guiltily. She couldn’t think of a good enough story to give him.

            Jimbo quickly turned back to her, then got on top of her, roughly holding her down by the arms. He squeezed her tight causing her to release a pathetic squeak of pain, which was his motive. He wanted her to know what a mistake she made. He would've preferred her reason to be a random one night stand due to being alone, or just plain horny, and him just being there at the right time, but that wasn't it, there was more to it and that frustrated him.

"S-stop..." Lisa stuttered, trying to muffle the fear in her voice and the readying tears.

"What, you thought I was just going to change my ways and treat you nicely like in some kind of fairytale? Well, girlie you have a lot to learn..." Jimbo could feel himself becoming aroused again with her quivering under him, he knew his anger was incoherent, but it felt familiar. This situation frustratingly reminded him of _her_. This wasn’t the same though, and decided that he was just going to fuck her again to put her in her place.

"Please, stop it... why are you doing this all of a sudden...?" Lisa whimpered.

"Funny, that's what I've been trying to ask you this whole time. For a nerd you're pretty stupid."

            Jimbo bolted up onto his knees, still on top of her. He smirked at her. She looked weak there under him all teary-eyed and exposed. He released the grip on one of her wrists while reaching down to pull his cock back out of his pants so he could fuck her again. Once Lisa noticed one of her wrists were free, and what he was trying to do she reached out and slapped him across the face, hard.

"Just stop it!" She snapped and started to cry.

            Jimbo looked away from her guiltily. He didn't understand why, but he did feel bad. He just wanted an answer out of her, which he still hadn't got. He didn't think he was any closer to getting an answer with him on top of her.

"You're a jerk..." She muttered, "I-I... just like you, okay?”

"Did you hit yourself on the head or somethin? You know who I am right? What I've done, how I live my life. You're either dense as fuck or crazy."

“I’m… not…” She couldn’t finish her sentence, just continued to cry more.

“Fine, let’s see how much you like me after this. Believe it or not I was actually being kinda gentle with you.” Jimbo smirked before pulling down his pants and entering her again.

            Lisa instantly knew what he meant by that statement since she felt more pain deep inside of her than during the previous round. He must’ve not been putting himself all the way into her before, because now she could feel him pound against her cervix. It was painful for her and she couldn’t believe he was able to get aroused that quickly again. He bit her neck and she yelped before moaning a bit. It was a strange mixture of pleasure and pain and she didn’t know if she liked or disliked it. This time it felt as if he was taking longer, but she thought it might just be because she wasn’t enjoying herself as much… He squeezed her tightly and pulled her hair as he shot his seed inside of her for a second time. She didn’t move or say anything, and looked away from him. He left her there without saying a word.


	3. Always

**Notes for the Chapter:**

> Yeah... I really suck at writing any sort of plot.

Chapter 3

            A week later Lisa found that she wasn’t feeling well. She was throwing up in the every morning. She started to become afraid of what it might mean, so she decided to bite the bullet and took a pregnancy test. The intimidating positive sign flashed bright pink back at her. She decided that she would have to confront Jimbo about this whether she liked it or not. Her head was pounding with anxiousness and worry.

            Lisa knew that it would be a bit of a challenge to find him since he never seemed to ever want to be found, but she was eventually able to find him after searching the places in town he frequented asked around. Lisa timidly walked up to him and told him that she needed to ask him a few questions in private. In exchange he just looked at her as if she were a freak.

“About us…” Lisa mumbled. 

“I don’t know what you’re talkin’ about.” Jimbo snapped back.

“You… never considered-“

“ _No_.” He interrupted and walked away from her. He didn’t want to hear another word from her.

            Lisa was left trembling as a tear ran down her cheek. She would have to use a backup plan; there was no other choice for her. Lisa went back home and sat at her desk for some time, writing a letter. A complicated letter containing everything she ever hid from Jimbo. She signed the letter, and stuffed it in an envelope labeled to him from her. She stuffed it in his mailbox and that was that, she would go through with the second part of her plan. She left out the part about her pregnancy in the letter. She didn’t want to grow up a single mother with a child with an unknown father. Instead, she decided to marry somebody she knew would accept her offer without batting an eye.

\---

            Jimbo left the envelope Lisa gave him on his side drawer for weeks without opening up, just occasionally glancing over at it once in a while. _Didn’t she end up marrying that nerd Van Houten? Must’ve been short lived whatever she had to say to me._ Jimbo thought angrily to himself as he held the envelope in his hand. _Just a typical woman, claiming to be in love then getting bored a few weeks later._ Jimbo sighed and ripped open the envelope.

            After reading the letter a few times he sat quietly on the side of his bed. How could he be so blind? He was such an idiot. Of course it was her…  He fell back onto his bed and lied there. He felt numb. _The last thing she wrote._

“I will love you always, and forever.”


End file.
